Director, Strategic Accounts - Toronto

About Decagon

Decagon is the leading conversational AI platform empowering every brand to deliver concierge customer experiences.

Our technology enables industry-defining enterprises like Avis Budget Group, Block’s Cash App and Square, Chime, Oura Health, and Hunter Douglas to deploy AI agents that power personalized, deeply satisfying interactions across voice, chat, email, SMS, and every other channel.

We’re building a future where customer experiences are being redefined from support tickets and hold music to faster resolutions, richer conversations, and deeper relationships. We’re proud to be backed by world-class investors who share that vision, including a16z, Accel, Bain Capital Ventures, Coatue, and Index Ventures, along with many others.

We’re an in-office company, driven by a shared commitment to excellence and velocity. Our values — Just Get It Done, Invent What Customers Want, Winner’s Mindset, and The Polymath Principle — shape how we work and grow as a team.

About the Role

We’re looking for a Strategic Account Executive that thrives in a highly autonomous environment. You’re product-minded, scrappy, and comfortable building your pipeline with some of the largest brands in the world. We have strong engineers on the team and the ability to aggressively support potential sales with customizations to close the deal.

In this role, you will

• Develop a strategy to break into and close key strategic logos for Decagon

• Develop deep, trusted relationships with key stakeholders at all levels of the customer organization (comfortable speaking to CX leaders, Product Leaders, and Operations Leaders)

• Understand the customer's business, challenges, and strategic priorities to uncover new opportunities for expansion

• Collaborate with internal teams (founders, deployment strategists, engineering, etc.) to deliver tailored solutions

• Forecast and accurately report on pipeline and revenue

• Develop and execute account plans to execute strategic deals

• Provide feedback and insights to product and leadership teams to influence the company's roadmap

• Maintain expert-level knowledge of the company's products, services, and industry trends

• Expect moderate travel.

Your background looks something like this

• 7+ years of experience in strategic or enterprise sales

• Proven track record of growing revenue and expanding business with large, complex accounts

• Excellent communication, presentation, and negotiation skills

• Strong business acumen and ability to speak the language of the C-suite

• Consultative selling approach with a focus on value-based solutions

• Ability to manage multiple stakeholders and cross-functional initiatives

• Bachelor's degree or equivalent work experience

Even better if you have

• Previous experience selling AI or customer support/experience software

Compensation

OTE $332,000 CAD - $415,000 CAD + Offers Equity

Benefits

We proudly offer the following benefits for our full-time employees:

• Medical, Dental, and Vision benefits for you and your family

• Life Insurance and Disability Benefits

• Retirement Plan (e.g., 401K, pension)

• Parental Leave

• Fertility and family building benefits through Carrot

• Monthly stipend to support your wellness, lifestyle, and work-life balance

• Daily lunches and snacks in the office to keep you at your best

• Take what you need vacation policy (subject to local requirements; UK employees receive 25 days of statutory leave)

These benefits are described in more detail in Decagon’s policies, may vary by location, and can change at any time according to applicable compensation and benefits plans.